Dataset for the Synthesis of Boron-Dipyrrin Dyes, their Fluorescent Properties, their Interaction with Proteins, Triton-X-Based Surfactants, and Micellar Clusterization Approaches to Validation based on Fluorescent Dyes
Scheme 1. Synthetic route for the tetra-substituted dyes. Scheme 2. Synthetic route to the meso-substituted dyes. Data for BODIPY synthesis (section 1: 1H-NMR, MALDI-TOF, UV-VIS, Elemental analysis) Tables of surfactants characteristics and titration data. Figure 1. DPM and BODIPY skeleton and quantum-chemically optimized molecule of mPB. Figure 2. BODIPY dyes and their optical characteristics + data table. Figure 3. Fluorescence and absorption spectra of the dyes in a binary mixture of THF:H2O 5:95 v/v at different concentrations; the relative changes in fluorescence and absorbance of the compounds as a function of the dye concentration + data table. Figure 4. Microscopy images of micellar clusters based on Triton-114 in the presence of Fe2+ and Ni2+ ions, with encapsulated Coumarin 6. The effect of BPhen chelator replacing. DLS spectra of TX-114 micelles, MCA, mPB-supported MCA, mPB-based MCCs, and MCC with encapsulated mPB + data table. Figure 5. Micelle models and archived CHARMM-GUI data files. Figure 7. Optical microscope images in transmitted light (top panel) and the corresponding images in the dark-field regime (bottom panel) during the first hour of the formation of BODIPYs in TX-100-based MCCs (A–G). The chemical structures of the dyes are shown on the top of microscopy images. Figure 8. CLSM images of TPB (λex = 547 nm, A) and mPB (λex = 488 nm, B) in MCCs during the first hour of formation. Figure 9. CLSM images (λex = 488 nm, insets) for (A) mNpB, (B) mDiPB, (C) mAB, and (D) mPB used as hydrophobic molecular support for the MCA after 10 min of formation. Figure 10. Changes in the fluorescence spectra of (A) mNpB, (B) mDiPB, (C) mAB, (D) mPB, (E) TMB, (F) TPB (solvent – EtOH), (G) TPB (solvent – THF), (H) aTPB during the titration of TX-114; the final concentrations of TX-114 in solution are (in mM): 1 – 0, 2 – 0.05, 3 – 0.1, 4 – 0.2, 5 – 0.5, 6 – 1, 7 – 2, 8 – 3, and 9 – 4, and the corresponding changes in the dye colors (A' – H') for their aqueous solutions in the absence (left cuvette) and in the presence of 4 mM (right cuvette) of TX-114 under daylight illumination (left image) and under irradiation of 365 nm UV light (right image). Figure 11. (A, B) The changes in the absolute and (C, D) normalized fluorescence for the dyes in the presence of TX-114 in normal (A, C) and a semi-log scale on the X-axis (B, D). Figure 12. Changes in the fluorescence spectra of mNpB (A), mDiPB (B), mAB (C), mPB (D), TMB (E), TPB (solvent – EtOH, F), TPB (solvent – THF, G), aTPB (H) in TX-114 (1.35 mM, black), after the addition of BPhen (MCA, red) and after the addition of a salt solution (MCCs, blue). Figure 13. Changes in the fluorescence spectra of MCAs supported by mAB (A), mPB (B), and TPB (C), and the relative changes in the fluorescence maxima for the investigated systems (D). Data are in archive format *.TGZ (WinRAR, 7Zip), *.XLS(X) and *.DOC(X) (MS Word, Excel) and in *.OPJ(U) (OriginPro), video files are in *.MP4 format file.
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Electronic absorption spectra were recorded using the Aquilon SF-104 (Russian Federation), the Agilent Cary 100 (USA), and the SOLAR SM2203 (Belarus). The fluorescence spectra have been taken using the Cary Eclipse (Varian-Agilent, USA-Australia; the detector voltage is 600 V), the Horiba Jobin Yvon Fluorolog 3, USA; the detector voltage is 950 V), and the SOLAR SM2203 (Belarus) spectrofluorometers. All experiments were performed in a thermostatic cell holder equipped with a Peltier PTC-2 heat transfer module at 298.2±0.1 K. Optical and fluorescence microscopy images were obtained using fluorescence microscopes using Micromed LUM-3 with a digital camera, ToupCam 5.0 MP CCD, and an Olympus BX-61 equipped with a QImaging MicroPublisher 3.3 digital camera. 1H-NMR spectra of the dyes were recorded on an Avance-500 (Bruker, Germany) spectrometer operating at 500 MHz. Elemental analysis was performed on a FLESH EA1112 (TermoQuest, Italy) elemental analyzer. MALDI-TOF analysis was performed on an AXIMA Confidence MALDI-TOF mass spectrometer (Shimadzu, Japan). Side UV illumination was applied using a UV lamp under a 254/365 nm exposure wavelength to obtain fluorescent images in the UV region. Quantum-chemical calculations have been done using Gaussian G09W, CHARMM. Molecular docking studies have been done using Autodock 4.2 (part of the MGLtools 1.5.7 package). Molecules have been visualized using PyMol 1.7, ChimeraX 1.4, Chimera 1.15, and Autodesk Fusion 360.